Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

Base Information

Chemical Name:Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate
CAS No.:137609-78-0
Molecular Formula:C₁₇H₃₀O₃Si
Molecular Weight:310.509
Hs Code.:

Synonyms:Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

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Chemical Property of Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

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Technology Process of Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

There total 17 articles about Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

: 137609-77-9
Ethyl (2E,5S)-8-Bromo-5<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2,8-nonadienoate

: 137609-78-0
Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

Guidance literature:: With potassium carbonate; palladium diacetate; triphenylphosphine; In acetonitrile; for 18h; Heating;
DOI:10.1021/jo00061a028

Reference yield:

: 137609-94-0
(2S,3S)-6-Bromo-2,3-epoxy-6-hepten-1-ol

: 137609-78-0
Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, - 78 deg C, 1 h, 2) RT, 1 h

2: NaH / tetrahydrofuran / 0.5 h / 0 °C

3: 87 percent / HCOOH, Et₃N / Pd₂(dba)3CHCl₃, n-Bu₃P / dioxane / 18 h / Ambient temperature

4: 99 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

5: 72 percent / K₂CO₃ / Pd(OAc)2, PPh₃ / acetonitrile / 18 h / Heating

With 1H-imidazole; formic acid; oxalyl dichloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; tributylphosphine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00061a028

Reference yield:

: 137609-95-1
(2R,3S)-3-(3-Bromo-but-3-enyl)-oxirane-2-carbaldehyde

: 137609-78-0
Ethyl <5S-(1E,5β)>-<5-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetate

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2: 87 percent / HCOOH, Et₃N / Pd₂(dba)3CHCl₃, n-Bu₃P / dioxane / 18 h / Ambient temperature

3: 99 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

4: 72 percent / K₂CO₃ / Pd(OAc)2, PPh₃ / acetonitrile / 18 h / Heating

With 1H-imidazole; formic acid; sodium hydride; potassium carbonate; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; tributylphosphine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00061a028